Polymerizable mesogenic cyclohexyl derivatives

a technology of cyclohexyl derivatives and mesogenic cyclohexyls, which is applied in the field of new polymerizable mesogenic or liquid crystalline compounds, can solve the problems of poor solubility, high melting point, and high value of prior art compounds

Inactive Publication Date: 2006-03-09
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0034] The invention further relates to the use of a compound of formula I, polymerizable material or polymer prepared thereof in optical films, polarizers, compensators, beam splitters, reflective films, alignment layers, colour filters, holographic elements, hot stamping foils, coloured images, decorative or security markings, liquid crystal pigments, adhesives, synthetic resins with anisotropic mechanical properties, cosmetics, diagnostics, nonlinear optics, optical information storage, as chiral dopants, in electronic devices like for example field effect transistors (FET) as components of integrated circuitry, as thin film transistors in flat panel display applications or for Radio Frequency Identification (RFID) tags, or in semiconducting components for organic light emitting diode (OLED) applications such as electroluminescent displays or backlights of e.g. liquid crystal displays, for photovoltaic or sensor devices, as electrode materials in batteries, as photoconductors, or for electrophotographic applications like electrophotographic recording.

Problems solved by technology

The polymerizable mesogenic compounds described in prior art, however, often exhibit LC phases only in a small temperature range or do not show mesophase behavior at all.
Another drawback for specific applications is that prior art compounds often exhibit high values of the birefringence.
The polymerizable mesogenic compounds described in prior art, however, do often exhibit high melting points, show poor solubility in low molar mass LC media or tend to negatively influence the LC and electrooptical properties of LC media.

Method used

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  • Polymerizable mesogenic cyclohexyl derivatives
  • Polymerizable mesogenic cyclohexyl derivatives
  • Polymerizable mesogenic cyclohexyl derivatives

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0127]

is prepared as follows:

[0128] Step 1:

[0129] Step 2:

[0130] Step 3:

[0131] Step 4:

Steps 1-4 have been described in the literature.

[0132] Step 5:

[0133] 36.6 g CCU-on-F (98% trans), 44.1 g cer(lIl)chlorid heptahydrate (99.9%, Aldrich) are dissolved in 300 ml methanol and 150 ml THF. At 0-10° C. 2.081 g solid NaBH4 (96%, Merck) is added portionwise. After the reaction is finished (5-20 min, DC-control) the mixture is quenched with 70 ml aq. ammonium chloride solution and 300 ml toluene are added. The mixture is filtered, the organic phase separated and the aqueous phase extracted with 100 ml toluene 3 times. The org. phases are dried, the solvent is evaporated and the residue recrystallized from heptane / toluene to give 32.6 g of a white solid (98.1% all-trans).

[0134] Step 6:

[0135] In a 500 ml four-neck flask 7.48 g DCC in 50 ml dichloromethane are added under a nitrogen atmosphere to a solution of 10.0 g CCU-ol-F, 117 mg DMAP and 7.36 g succinic acid mono-[2-(2-meth...

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Abstract

The invention relates to new polymerizable mesogenic or liquid crystalline compounds comprising a terminal cyclohexylphenyl group wherein the phenyl group has polar substituents, to polymerizable mesogenic or liquid crystalline mixtures and anisotropic polymers prepared thereof, and to the use of the new compounds and the mixtures and polymers prepared thereof in optical and electrooptical devices, adhesives, synthetic resins with anisotropic mechanical properties, cosmetics, diagnostics, liquid crystal pigments, decorative and security applications, nonlinear optics, optical information storage, electronic devices like organic field effect transistors (FET or OFET) or electroluminescent devices.

Description

FIELD OF THE INVENTION [0001] The invention relates to new polymerizable mesogenic or liquid crystalline compounds comprising a terminal cyclohexylphenyl group wherein the phenyl group has polar substituents, to polymerizable mesogenic or liquid crystalline mixtures and anisotropic polymers prepared thereof, and to the use of the new compounds and the mixtures and polymers prepared thereof in optical and electrooptical devices, adhesives, synthetic resins with anisotropic mechanical properties, cosmetics, diagnostics, liquid crystal pigments, decorative and security applications, nonlinear optics, optical information storage, electronic devices like organic field effect transistors (FET or OFET) or electroluminescent devices. BACKGROUND AND PRIOR ART [0002] Polymerizable mesogenic or liquid crystal (LC) compounds, which are also known as reactive mesogens (RM), have been described in prior art for various purposes. For example, they can be used for the preparation of linear or cross...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C09K19/30C07C25/13C09K19/38C09K19/20
CPCC09K19/3003C09K19/3852C09K2019/0448Y10T428/10C09K2019/3009C09K2019/301C09K2019/3095C09K2019/0496C09K2323/00
Inventor KLEIN, MARKUSDEROW, STEPHAN
Owner MERCK PATENT GMBH
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